Triethylamine → HCID 58204112, compound

HRID 1190678Notes

Reaction equation

HRID 1190678 reaction equation
OC(C(F)(F)F)=O.[CH:8]([N:11]1[C:15]([C:16]2[S:17][C:18]3[CH2:19][CH2:20][O:21][C:22]4[CH:29]=[C:28]([CH:30]5[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]5)[CH:27]=[CH:26][C:23]=4[C:24]=3[N:25]=2)=[N:14][CH:13]=[N:12]1)([CH3:10])[CH3:9].C(N(CC)CC)C.Br[CH2:44][C:45]([NH2:47])=[O:46]>C(Cl)Cl.CO.O>[CH:8]([N:11]1[C:15]([C:16]2[S:17][C:18]3[CH2:19][CH2:20][O:21][C:22]4[CH:29]=[C:28]([CH:30]5[CH2:35][CH2:34][N:33]([CH2:44][C:45]([NH2:47])=[O:46])[CH2:32][CH2:31]5)[CH:27]=[CH:26][C:23]=4[C:24]=3[N:25]=2)=[N:14][CH:13]=[N:12]1)([CH3:10])[CH3:9]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 696322-BromoacetamideHCID 866523172-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-8-piperidin-4-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene TFA salt

Product 1

HCID 58204112HCID 58204112, compoundYield 72.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-8-piperidin-4-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene TFA salt 375 (250 mg, 0.49 mmol) in DCM (2.5 mL) was added triethylamine (157 μL, 1.13 mmol) followed by 2-bromoacetamide (81 mg, 0.59 mmol). The reaction mixture was stirred for 42 hours before being diluted with MeOH and water. The DCM was removed in vacuo to give a suspension. The solid was filtered off and washed with MeOH then ether to give 475 as an off-white solid (160 mg, 72%). LCMS: RT=3.17 min, [M+H]+=453. 1H NMR δ (ppm) (DMSO-d6): 8.23 (1H, d, J=8.20 Hz), 8.05 (1H, s), 7.17 (1H, s), 7.08 (1H, s), 7.07-7.02 (1H, m), 6.90 (1H, d, J=1.75 Hz), 5.81-5.71 (1H, m), 4.35-4.28 (2H, m), 3.37 (2H, s), 2.90-2.79 (4H, m), 2.13 (2H, dd, J=8.92, 8.51 Hz), 1.77-1.67 (4H, m), 1.50 (6H, d, J=6.58 Hz). 1 Proton obscured by solvent peaks

Workup

  1. customThe DCM was removed in vacuo
  2. customto give a suspension
  3. filtrationThe solid was filtered off
  4. washwashed with MeOH

Sources & evidence

ORD record
ord-a0c3a3cf51ac483f855e47da99e28479
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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